Beta-amino ester gas hydrate inhibitors

1. A compound of formula (IV) or (VI),

wherein

R 1 is unsubstitued alkyl, or unsubstituted alkenyl;

R 2 is substituted or unsubstituted alkyl or substituted or unsubstituted alkenyl;

R 3 is hydrogen or substituted or unsubstituted alkyl;

R 4 is unsubstitued alkyl, or unsubstitued alkenyl;

X − is a counterion;

m is any one of an integer from 1 to 100.

2. The compound of claim 1 , wherein

R 1 is unsubstituted C 1 -C 22 alkyl or unsubstituted C 2 -C 22 alkenyl;

R 2 is hydrogen or unsubstituted C 1 -C 6 alkyl;

R 3 is hydrogen or unsubstituted C 1 -C 6 alkyl;

R 4 is unsubstituted C 1 -C 6 alkyl; and

m is any one of an integer from 1 to 20.

3. The compound of claim 1 , wherein R 3 is hydrogen.

4. The compound of claim 1 , wherein m is 2, 4, 10, or 20.

5. The compound of claim 1 , wherein R 1 is —C 12 H 25 , —C 18 H 37 , or —C 18 H 35 .

6. The compound of claim 1 , having the formula (V),

7. The compound of claim 6 , wherein

R 1 is —(CH 2 ) 11 CH 3 , —(CH 2 ) 17 CH 3 , or —(CH 2 ) 8 CH═CH(CH 2 ) 7 CH 3 ;

R 2 is —(CH 2 ) 3 CH 3 , or —(CH 2 ) 5 CH 3 ; and

X − is bromide.

8. The compound of claim 7 , wherein m is 2, 4, 10, or 20.

9. The compound of claim 1 , selected from the group consisting of:

3,6,9,12-tetraoxatetracosyl 3-(4-methylpiperazin-1-yl)propanoate;

1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16-pentaoxaoctacosyl)piperazin-1-ium bromide;

1-hexyl-1-methyl-4-(3-oxo-4,7,10,13,16-pentaoxaoctacosyl)piperazin-1-ium bromide;

(Z)-2-(2-(octadec-9-enyloxy)ethoxy)ethyl 3-(4-methylpiperazin-1-yl)propanoate;

(Z)-1-butyl-1-methyl-4-(3-(2-(2-(octadec-9-enyloxy)ethoxy)ethoxy)-3-oxopropyl)piperazin-1-ium bromide;

(Z)-1-hexyl-1-methyl-4-(3-(2-(2-(octadec-9-enyloxy)ethoxy)ethoxy)-3-oxopropyl)piperazin-1-ium bromide;

3,6,9,12,15,18,21,24,27,30-decaoxaoctatetracontyl 3-(4-methylpiperazin-1-yl)propanoate;

1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34-undecaoxadopentacontyl)piperazin-1-ium bromide;

1-hexyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34-undecaoxadopentacontyl)piperazin-1-ium bromide;

3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60-icosaoxaoctaheptacontyl 3-(4-methylpiperazin-1-yl)propanoate;

1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64-henicosaoxadooctacontyl)piperazin-1-ium bromide;

1-hexyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64-henicosaoxadooctacontyl)piperazin-1-ium bromide;

(Z)-3,6,9,12,15,18,21,24,27,30-decaoxaoctatetracont-39-enyl 3-(4-methylpiperazin-1-yl)propanoate;

(Z)-1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34-undecaoxadopentacont-43-enyl)piperazin-1-ium bromide;

(Z)-1-hexyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34-undecaoxadopentacont-43-enyl)piperazin-1-ium bromide;

(Z)-3,6,9,12,15,18,21,24,27,30,33,36,39,42,45,48,51,54,57,60-icosaoxaoctaheptacont-69-enyl 3-(4-methylpiperazin-1-yl)propanoate;

(Z)-1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64-henicosaoxadooctacont-73-enyl)piperazin-1-ium bromide; and

(Z)-1-hexyl-1-methyl-4-(3-oxo-4,10,13,16,19,22,25,28,31,34,37,40,43,46,49,52,55,58,61,64-henicosaoxadooctacont-73-enyl)piperazin-1-ium bromide.

10. The compound of claim 1 , having the formula (IV)

R 1 is —(CH 2 ) 11 CH 3 , —(CH 2 ) 17 CH 3 , or —(CH 2 ) 8 CH═CH(CH 2 ) 7 CH 3 ;

R 2 is —(CH 2 ) 3 CH 3 , or —(CH 2 ) 5 CH 3 ; and

R 3 is hydrogen or methyl.

11. The compound of claim 1 , having the formula (VI)

R 1 is —(CH 2 ) 11 CH 3 , —(CH 2 ) 17 CH 3 , or —(CH 2 ) 8 CH═CH(CH 2 ) 7 CH 3 ;

R 4 is —(CH 2 ) 3 CH 3 , or —(CH 2 ) 5 CH 3 ; and

R 3 is hydrogen or methyl.

12. The compound of claim 9 , selected from the group consisting of:

1-butyl-1-methyl-4-(3-oxo-4,7,10,13,16-pentaoxaoctacosyl)piperazin-1-ium bromide;

1-hexyl-1-methyl-4-(3-oxo-4,7,10,13,16-pentaoxaoctacosyl)piperazin-1-ium bromide; and

(Z)-1-hexyl-1-methyl-4-(3-(2-(2-(octadec-9-enyloxy)ethoxy)ethoxy)-3-oxopropyl)piperazin-1-ium bromide.

13. A composition comprising a mixture of compounds of formula (IV) or (VI) of claim 1 .

14. The composition of claim 13 , further comprising one or more additives independently selected from the group consisting of a synergistic compound, an asphaltene inhibitor, a paraffin inhibitor, a corrosion inhibitor, a scale inhibitor, an emulsifier, a water clarifier, a dispersant, an emulsion breaker, a hydrogen sulfide scavenger, a gas hydrate inhibitor, a biocide, a pH modifier, a surfactant, and a solvent.

15. The composition of claim 14 , comprising at least one solvent.

16. The composition of claim 15 , wherein the solvent is isopropanol, methanol, ethanol, heavy aromatic naptha, toluene, ethylene glycol, ethylene glycol monobutyl ether (EGMBE), diethylene glycol monoethyl ether, xylene, kerosene, diesel, isobutanol, heptane, or a combination thereof.

17. A method of inhibiting the formation of hydrate agglomerates in a fluid comprising water, gas, and optionally liquid hydrocarbon, the method comprising adding to the fluid an effective amount of a composition comprising one or more compounds of formula (IV) or (VI) according to claim 1 .

18. The method of claim 17 , wherein said fluid has a salinity of 1 to 20 w/w percent total dissolved solids (TDS).

19. The method of claim 17 , wherein said fluid has a water cut from 1 to 65 v/v percent.

20. The method of claim 17 , wherein the fluid is contained in an oil or gas pipeline.